Five Rivers: Wisconsin and Minnesota Biking Adventure

There are basically two types of people. People who accomplish things, and people who claim to have accomplished things. The first group is less crowded.”

Mark Twain

Join us as we enjoy five days of beautiful riding along five scenic rivers, using seven different bicycle trails, coasting through no fewer than 20 small towns, and making use of over 120 miles of mostly paved, car-free bicycle paths on both sides of the Mississippi River in Wisconsin and Minnesota. How is that for accomplishment?

If you ride the main routes each day, you will ride from inn to inn, never having to see the inside of our support vehicle. The scenery is vast and varied: open prairies, small streams, limestone bluffs, dark forests, cute small towns, railroad tunnels, and of course the mighty Mississippi River.

The bicycling is the highlight of this tour. This area, called the Driftless Area, was the only part of either Wisconsin or Minnesota to not be covered by the last ice age, which means the region retained the hilly nature the rest of the Midwest lost. However, by riding on trails made from old railroad beds we get all the scenery and little of the hill climbing. In fact, 85% of our riding is on car-free, scenic, mostly flat trails with the remainder on country roads. We spend the first two days in Wisconsin on a total of six different rail trails riding along the La Crosse, Kickapoo, and Trempeleau rivers. We then cross the Mississippi and spend half a day cycling on low-traffic, country roads as we connect to the amazing Root River Trail and the Harmony – Preston Valley Trail in southern Minnesota.

We also love the small towns we pass through each day and stay in each night. Granted, some of the towns are not known for luxury accommodations or fancy meals. But La Crosse, Wisconsin is a classic Mississippi River town and Lanesboro, Minnesota, is one of the cutest small towns in America – both filled with Midwest-nice, welcoming locals. We are discerning with our lodging choices and experience some of the best that small-town Wisconsin and Minnesota have to offer.

These areas are famous to locals and to bike enthusiasts from afar, yet relatively unknown to the general public. Come see why biking this area is an accomplishment of which Mark Twain would be proud.

Private Tour Info

Want to make this trip even more memorable? Grab your friends and pick a date.

Start planning your private tour


Other Info: Bike rental is a $35/day additional charge. E-bikes can be rented for $75/day.

Book this Tour

Trip Highlights

  • Bike the amazing Root River Trail network, one of the finest bike tour locations in the country
  • Stay in small-town Lanesboro, Minnesota, rated one of the top arts, sports, and overall small towns in America
  • Ride the Elroy - Sparta Trail, the first converted rail trail in the country
  • Visit the classic Mississippi River town of La Crosse, Wisconsin and take a paddleboat cruise on the river
  • Ride through long, dark, and fun abandoned railroad tunnels en route

We meet after lunch in Sparta, Wisconsin, the self-proclaimed Bicycle Capital of America and our home for the night. We'll have an introductory talk and, if you are renting a bicycle, fit it to you. Our first ride takes us on the famous Elroy-Sparta Trail. This trail is considered the first converted rail trail in the country, starting a movement that now boasts over 24,000 miles of rail trails in the US alone! In 1964, trains were still running but by the next year, the Elroy-Sparta trail was already in progress. The full trail end-to-end is 32.5 miles long, crosses over the Kickapoo River, and has three exciting railroad tunnels, all over 140 years old, two that are 1/4 mile long and one that is a full three quarters of a mile. We will be going through two of these tunnels on our ride - you will want to bring a headlamp and perhaps even a jacket!

Distance: 20 or 40 Miles


From Sparta we head west, changing both rivers and trails. We are now following the La Crosse River and cycling on the La Crosse Trail, a continuation of the same Chicago to Minneapolis railroad route. We'll pass through hardwood forests, wetlands, and agricultural lands. En route, you can choose to stop at the Le Coulee Cheese Castle, where you can purchase over 50 varieties of Wisconsin cheese. It might make for a good picnic along the path. The trail ends in the small city of La Crosse, Wisconsin, on the banks of the Mississippi River.  You'll then have the choice to add on more miles along the Great River Trail or you can hop off your bike and trade your wheels for an authentic river paddleboat and take a sightseeing cruise on the Mississippi River. Our hotel is right on Riverfront Park and we are within walking distance of a wine bar, distillery, and plenty of shops. This evening, we'll walk to dinner at one of La Crosse's excellent restaurants.

Distances: 29, 41, or 64 Miles


Today we ride a short distance along the Mississippi River before crossing this mighty barrier that divides east from west, departing Wisconsin and entering Minnesota. This is the only day of the tour we are not riding the whole time on a rail trail to get to our next destination. The routes are scenic if a bit hillier than the rest of our tour days. In Minnesota, we pass through the town of La Crescent and then head up one of the famous bluffs that line the Mississippi. Once we are on top, our cycling is much easier as we make our way through rural America and on down to our home for the night in Rushford, Minnesota. Once we get to the town of Houston, you'll have the choice of shuttling to our hotel, hopping on the Root River Trail and riding to Rushford, or - if you are looking for longer mileage - extending your ride to the small town of Caledonia, Minnesota where you can have lunch at the Farmhouse Eatery, located in a Victorian home in the heart of town.

Distances: 22, 35, or 66 Miles


Today we continue to ride on one of the best trail networks in the country, the Root River Trail. The trail is paved, making for smooth and fast riding. We follow the Root River for the entire morning, giving us scenic views of the riverscape and limestone bluffs above. En route, you can stop for pie at the Aroma Pie Shoppe in Whalan, one of the storied stops of the trail. However, the highlight of the day might actually be at the finish when we reach Lanesboro. We love Lanesboro, one of the cutest small towns in America! It has outdoor recreation, art galleries, fun restaurants, nice lodging, and even the high-quality Commonwealth Theater. Lanesboro makes for a perfect last stop on the tour. If you need some extra mileage, you can continue on the southern branch of the trail network, cycling from Lanesboro south to Preston or even Harmony, a town famous for its Amish residents. This evening, we'll have a nice final dinner to celebrate our accomplishments!

Distances: 19, 40, or 64 Miles


But we are not done! We still have time for a final ride on the western spur of the Root River Trail Network. We'll cycle to trail's end in Fountain, riding along the river and then passing through open agricultural lands, and back to Lanesboro in time to shower and check out.

Distances: 9 or 22 Miles

Book this Tour

Trip Accommodations


The hotel is not fancy but gets great reviews and is the top-rated hotel in Sparta. We'll enjoy comfortable accommodations that will allow us to catch a good night's sleep after our first day on the trails.


The GrandStay Hotel is perfectly situated on Riverfront Park and just steps from the rolling Mississippi River. While not cycling, you can stroll along the river through a beautiful international garden. Otherwise, you can walk the historic streets of downtown, perhaps visiting the La Crosse Distilling Company or 4 Sisters Wine Bar.


Just steps from the scenic Root River State Trail and within easy access of the beautiful Root River, the Loken's Rushford Inn offers convenient, comfortable accommodations after a day on the trails. With its spacious rooms and excellent service, one hospitality professional called it "The best small town hotel I have ever stayed in over the past 30-years."


Stone Mill Suites is housed in a building originally constructed in 1885 from limestone quarried from bluffs along the Root River. We love this hotel for its history combined with modern conveniences and friendly owners. We also use an additional hotel right across the street called The Cottage House Inn. It is family-built, owned and operated and you probably won’t find a friendlier spot. You’ll feel right at home relaxing on the front porch, watching small-town American life!

Book this Tour
Arrival & Departure

If you are driving to the tour, we will meet you just after lunch in Sparta, Wisconsin. We finish with a final bike ride and shower in the morning of the last day in Lanesboro, Minnesota and will shuttle you back to your car after lunch. If you are flying to the tour, you should fly into Minneapolis - St. Paul Airport and take the Groome Shuttle to Rochester, Minnesota the evening before. We will pick you up in the morning of the first day to shuttle you to Sparta and will shuttle you back to Rochester on the final morning. Alternatively, you could rent a car after flying into Milwaukee or Madison, drive to Sparta, and leave your car there.

What's Included?
  • At least two Zephyr guides accompany each trip and a third is added as necessary.
  • Double occupancy lodging is included. If you are traveling solo, we will match you with another traveler of the same gender. However, you may pay a single supplement to have your own room.
  • All of your dinners and breakfasts are included. Gratuity for these meals is also included. In general, we leave lunches open so that you have time to explore and enjoy the local flavors en route.
  • All your transportation is included once you meet your guides on the first day.
  • All trail fees and permits are included.
  • NOT INCLUDED Beverages, desserts, lunches, gratuities to your guides, personal expenses and travel to and from the destination.

Minnesota and Wisconsin have a long winter and a hot and muggy summer. September is an outstanding time to visit, with usually warm days but reduced humidity. However, be prepared for all types of weather as we ride each day no matter what! (Also - you'll want to make sure to bring a light jacket for the tunnels on Day 1's ride on the Elroy-Sparta Trail.)

Extending Your Stay

If you are driving or renting a car, it is not far to Minneapolis or the college and capital city of Madison, Wisconsin. A bit farther north, the lakes area of Minnesota is spectacular and Duluth on the shores of Lake Superior is a fun small city.

Changes to Your Itinerary

While everything under “What is Included” will remain the same, the actual restaurants, hotels, and activities listed in our itineraries are subject to modifications. Changes that are out of our control are common – a restaurant closes or loses its awesome chef, a winery changes its visiting hours, a hotel gets remodeled, a road or trail undergoes construction. You are entrusting us to create an outstanding vacation for you and so it is possible we may take the liberty of making necessary changes (even at the last minute, during the guides’ scout trip) to the itinerary that will improve your overall trip experience. If there is any one experience that is going to make or break your trip, please discuss this with us in advance! We will attempt to keep our website itinerary as current as possible and communicate any major changes with you in the weeks prior to the tour.


Book this Tour

I'm Interested

I really want to join this trip but can't book quite yet. Put me on the Interested List.

More Information

I'm interested in this tour and want more information. Get in touch with us.

Plan a Private Tour

Looking to book this itinerary as a private tour? Complete our private tour inquiry form to get started.

Get Travel Inspiration Delivered Directly to Your Inbox

Sign up for our newsletter to receive regular updates on our upcoming adventures.

  • Hidden